DE199979C - - Google Patents
Info
- Publication number
- DE199979C DE199979C DE1907199979D DE199979DA DE199979C DE 199979 C DE199979 C DE 199979C DE 1907199979 D DE1907199979 D DE 1907199979D DE 199979D A DE199979D A DE 199979DA DE 199979 C DE199979 C DE 199979C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- green
- jvo
- yellow
- blackish
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 19
- 239000000975 dye Substances 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 229920001021 polysulfide Polymers 0.000 claims description 4
- 239000005077 polysulfide Substances 0.000 claims description 3
- 150000008117 polysulfides Polymers 0.000 claims description 3
- 239000000988 sulfur dye Substances 0.000 claims description 3
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 2
- HFVSZZBTJBGNDU-UHFFFAOYSA-N 5-methyl-1,5-dinitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1(C)CC([N+]([O-])=O)=CC=C1 HFVSZZBTJBGNDU-UHFFFAOYSA-N 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KFRLDGDNVDFWRP-UHFFFAOYSA-N 2,3-dinitro-n-phenylaniline Chemical compound [O-][N+](=O)C1=CC=CC(NC=2C=CC=CC=2)=C1[N+]([O-])=O KFRLDGDNVDFWRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000155 melt Substances 0.000 description 3
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000189705 Dunedin group Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B49/00—Sulfur dyes
- C09B49/02—Sulfur dyes from nitro compounds of the benzene, naphthalene or anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-■Ja 199979"-KLASSE 22 d. GRUPPE - ■ Yes 199979 "CLASS 22 d. GROUP
Verfahren zur Darstellung von braunen Schwefelfarbstoffen.Process for the preparation of brown sulfur dyes.
Werden aromatische m-Dinitrokörper, welche keine Hydroxylgruppe enthalten, wie Dinitrobenzol, Dinitrochlorbenzol 4 : 2 : 1, Bisdinitrophenyldisulfid oder ihre Reduktionsprodukte mit Polysulfid verschmolzen, so entstehen schwach graugrüne bis schwärzlichgrüne Farbstoffe. Ebenso gibt Glycerin, mit Polysulfid auf höhere Temperatur erhitzt, einen wertlosen olivgrauen Farbstoff.Are aromatic m-dinitro bodies that do not contain a hydroxyl group, such as dinitrobenzene, Dinitrochlorobenzene 4: 2: 1, bisdinitrophenyl disulfide or their reduction products fused with polysulphide, pale gray-green to blackish-green results Dyes. Likewise, glycerine, heated to a higher temperature with polysulfide, gives one worthless olive gray dye.
Es wurde nun die überraschende und nicht vorauszusehende Beobachtung gemacht, daß Gemische von aromatischen Dinitrokörpern, welche keine Hydroxylgruppe enthalten, bzw. ihre Reduktionsprodukte und Glycerin imThe surprising and unforeseeable observation has now been made that Mixtures of aromatic dinitro bodies which do not contain a hydroxyl group or their reduction products and glycerine im
.15 Verhältnis von 1 zu ]/2 bis 1 Molekül bei dem Schwefelungsprozeß braune, intensive Farbstoffe liefern, welche ein vorzügliches Egalisierungsvermögen ,und sehr gute Echtheitseigenschaften besitzen..15 ratio of 1 to ] / 2 to 1 molecule in the sulphurisation process yield brown, intense dyes which have excellent leveling properties and very good fastness properties.
Das Glycerin dient hierbei nicht als Verdünnungsmittel der Schmelze, wie in früheren Patentschriften wiederholt beschrieben, sondern es nimmt an der Reaktion teil.The glycerine does not serve as a diluent for the melt, as in earlier versions Patent specifications described repeatedly, but it takes part in the reaction.
In eine Polysulfidschmelze von 2000 Teilen kristallisiertem Schwefelnatrium und 500Teilen Schwefel trägt man unter Umrühren 500 Teile Dinitrochlorbenzol und 230 Teile Glycerin ein.In a polysulfide melt of 2000 parts of crystallized sodium sulphide and 500 parts 500 parts of dinitrochlorobenzene and 230 parts of glycerol are introduced with stirring.
Nach beendigter Reaktion wird das Ölbad langsam auf 200° geheizt und bei dieser Temperatur 4 bis 5 Stunden lang gehalten.After the reaction has ended, the oil bath is slowly heated to 200 ° and at this point Maintained temperature for 4 to 5 hours.
Hierauf wird die Schmelze noch 4 Stunden bei 235.bis 2400 im Backofen erhitzt.The melt is then heated in the oven at 235 to 240 0 for a further 4 hours.
Der Farbstoff wird nach dem Erkalten zerkleinert und bildet ein graubraunes Pulver, 40 The dye is crushed after cooling and forms a gray-brown powder, 40
welches sich' leicht in Wasser löst und ungeheizte Baumwolle in lebhaften braunen Tönen mit rötlichgelbem Überschein anfärbt.which dissolves easily in water and unheated cotton in vivid brown tones stained with reddish yellow overtones.
Der Farbstoff ist chlorfrei.The dye is chlorine-free.
In analoger Weise werden andere Dinitrokörper ohne Hydroxylgruppe verschmolzen. Dabei können die Mengen von Schwefel und Schwefelnatrium zu dem Ausgangsmaterial in weiten Grenzen abgeändert werden, ohne wesentlich andere Resultate zu erzielen. Die Schmelze kann auch unter Zusatz von Schwermetallsalzen, wie Kupfersulfat und Chlorzink, ausgeführt werden, die Nuance wird dadurch etwas voller und blumiger, während die Echtheitseigenschaften im allgemeinen die gleichen bleiben.Other dinitro bodies without a hydroxyl group are fused in an analogous manner. The amounts of sulfur and sodium sulfur can add to the starting material can be varied within wide limits without significantly different results to achieve. The melt can also be made with the addition of heavy metal salts, such as copper sulfate and zinc chloride, which makes the shade a bit fuller and more flowery, while enhancing the fastness properties generally stay the same.
In der umstehenden Tabelle sind die färberischen Eigenschaften einiger aus aromatischen Dinitroverbindungen, welche keine Hydroxylgruppe enthalten, nach vorliegendem Verfahren darstellbaren Farbstoffe angeführt.In the table below are the coloring properties of some of the aromatic Dinitro compounds which do not contain a hydroxyl group according to the present Process representable dyes listed.
Nach der französischen Patentschrift 300983 wird aus m-Dinitrotoluol zwar ein brauner Schwefelfarbstoff erhalten, welcher jedoch von dem unter Zusatz von Glycerin hergestellten durch lebhaften und rötlichen Ton sowie durch seine Intensität weit übertroffen wird.According to French patent specification 300983, m-dinitrotoluene turns into a brown one Sulfur dye obtained, which, however, from that produced with the addition of glycerol is far surpassed by its lively and reddish tone and its intensity.
Claims (1)
Farbstoff färbtMelt without glycerine.
Dye stains
Farbstoff färbtMelt with glycerin.
Dye stains
Überscheinbrown with yellow
Oversight
rötlichem Überscheinbrown with very lively
reddish shine
Überscheinbrown with yellow
Oversight
JV O2 -<^ y~ JV y-( y
I
JVO3 Dinitrodiphenylamine
JV O 2 - <^ y ~ JV y- (y
I.
JVO 3
JV O2 -<^ y~S - S-ζ y~ JV O2
I I
JVO2 JVO2 Bisdinitrophenyl disulfide.
JV O 2 - <^ y ~ S - S-ζ y ~ JV O 2
II
JVO 2 JVO 2
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT40172D AT40172B (en) | 1907-08-14 | 1908-07-29 | Process for the preparation of brown sulfur dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE199979C true DE199979C (en) |
Family
ID=462650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907199979D Expired - Lifetime DE199979C (en) | 1907-08-14 | 1907-08-14 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE199979C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958585C (en) * | 1953-11-22 | 1957-02-21 | Hermann Rath Dipl Chem Dr | Process for the production of water-soluble sulfur dyes |
-
1907
- 1907-08-14 DE DE1907199979D patent/DE199979C/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958585C (en) * | 1953-11-22 | 1957-02-21 | Hermann Rath Dipl Chem Dr | Process for the production of water-soluble sulfur dyes |
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